Tag: M.W=100-200

Electric Literature of 19047-31-5,Some common heterocyclic compound, 19047-31-5, name is 2-Chloro-N-cyclopropylacetamide, molecular formula is C5H8ClNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A solution of 2-chloro-N-cyclopropylacetamide (1.33 g, 10 mmol), 3- bromobenzenethiol (1.6 g, 8.5 mmol) and K2CO3 (4.8 g, 35 mmol) in 30 mL of acetone was heated at 70 C overnight. The mixture was filtered and concentrated to give a residue, which was purified by column chromatography (PE/EA, 1/1) to give the title compound (2.4 g, 96%) as a white solid. 1H NMR delta (300 MHz, CDC13) 7.39 (1H, m), 7.31 (1H, m), 7.14 (2H, m), 6.71 (1H, s), 3.58 (2H, s), 2.64-2.77 (1H, m), 0.73-0.84 (2H, m), 0.41 (2H, m); m/e 286 (M+H)+.

The synthetic route of 19047-31-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KADMON CORPORATION, LLC; BOXER, Michael; RYAN, John; TONRA, James; WO2014/55999; (2014); A2;,
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Reference of 16066-84-5, A common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, molecular formula is C6H13NO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 1 Preparation of Compound c71 (0551) Compound c70 (1.0g, 4.15mmol) was dissolved in dioxane (16mL), and tertiary butyl methyl carbamate (653mg, 4.98mmol), 2- dicyclohexylphosphino-2 ‘, 4′ , 6’-triisopropyl-biphenyl (297mg, 0.622mmol), potassium phosphate (2.20g, 10.73mmol) and tris (dibenzylideneacetone) palladium (190mg, 0.207mmol) were added to the mixture at 100 C for 5 hours. Tertiary butyl methyl carbamate (218mg, 1.66mmol), 2-dicyclohexylphosphino-2 ‘, 4′, 6’-triisopropyl biphenyl (99mg, 0.207mmol), potassium phosphate (0.73g, 3.57mmol) and tris (dibenzylideneacetone) palladium (0) (63.3mg, 0.069mmol) were added to the mixture and the mixture was stirred for 3 hours. Tertiary butyl methyl carbamate (435mg, 3.32mmol), 2- dicyclohexylphosphino-2 ‘, 4′, 6’-triisopropyl biphenyl (99mg, 0.207mmol) and tris (dibenzylideneacetone) palladium (0) (63.3mg, 0.069mmol) was then added to the mixture and the mixture was stirred for 5.5 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give compound c71 (0.75g, 74% yield). [M + H] = 244.95, Method Condition 3: retention time 2.08 min

The synthetic route of 16066-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; KOBAYASHI, Naotake; ASAHI, Kentarou; TOMIDA, Yutaka; OHDAN, Masahide; FUMOTO, Masataka; SASAKI, Yoshikazu; KURAHASHI, Kana; INOUE, Takatsugu; URABE, Tomomi; NISHIURA, Yuji; IWATSU, Masafumi; MIYAZAKI, Keisuke; OHYABU, Naoki; WADA, Toshihiro; KATOU, Manabu; (276 pag.)EP3059225; (2016); A1;,
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Synthetic Route of 103361-99-5,Some common heterocyclic compound, 103361-99-5, name is 7-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, molecular formula is C8H6FNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 2H-1 ,4-benzothiazin-3(4H)-one (intermediate 33, 3.1 g, 18.55 mmol) in dry Toluene (15 mL) in a glass tube was added Lawesson’s reagent (4.50 g, 1 1 .13 mmol, 0.6 eqv) and the mixture reacted in a microwave reactor at 100 C for 5 minutes). Cyclohexane was added, and the resulting solid was filtered. The solid was dissolved in Et^O and the solvent removed not quite to dryness. This concentrated mixture was purified using a Biotage SP1 purification system using Normal phase Silica SNAP 4×50 g (because of low solubility) column in the gradient of ethyl acetate in cyclohexane (8 % in 1 CV, 8-30 % in 10 CV, 30-66 % in 10 CV) to give the title compound (2 g); m/z (ES): 184.10 [M+H]+; 1H NMR (600 MHz, DMSO-d6) delta ppm 4.86 (s, 2 H) 6.84 – 6.88 (m, 1 H) 6.92 – 6.97 (m, 1 H) 7.07 – 7.1 1 (m, 1 H) 12.77 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; BERTANI, Barbara; CREMONESI, Susanna; GARZYA, Vincenzo; MICHELI, Fabrizio; RUPCIC, Renata; SABBATINI, Fabio Maria; WO2011/151361; (2011); A1;,
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Some common heterocyclic compound, 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide, molecular formula is C9H10ClNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 2-Chloro-N-(3-methoxyphenyl)acetamide

General procedure: A mixture of the potassium salt 22 (1.5g, 0.01mol) and the appropriate chloroacetanilides (0.01mol) namely, 2-chloro-N-(3-methoxyphenyl)acetamide and 2-chloro-N- (4-fluorophenyl)acetamide in dry DMF (20ml) was heated over a water bath for 3h. The reaction mixture was then cooled, poured into ice-cooled water (150ml) and stirred well for 30min. The solid such separated was filtered, washed with water, dried and crystallized from methanol/toluene mixture (1:1) to afford the corresponding compounds 25a – b, respectively. 2-(Bis[1,2,4]triazolo[4,3-a:3?,4?-c]quinoxalin-3-ylsulfanyl)-N-(3-methoxyphenyl) acetamide (25a). White crystal (yield 71 %); m. p. 256 – 259 C; IR (KBr, cm1); 3264 (NH), 3077 (CH aromatic), 2950 (CH aliphatic), 1689 (C=O amide); 1H NMR (DMSO-d6) delta ppm: 3.70 (s, 3H, -OCH3), 4.52 (s, 2H, CH2), 6.62 (d, 1H, J=8.1Hz, Ar-H, H-4 of phenyl), 6.69 (d, 1H, J=8.4Hz, Ar-H, H-6 of phenyl), 7.20 (dd, 1H, J=8.1, 8.4Hz, Ar-H, H-5 of phenyl), 7.23 (s, 1H, Ar-H, H-2 of phenyl), 7.72 (dd, 1H, J=7.8, 8.4Hz, Ar-H, H-7 of quinoxaline), 7.74 (dd, 1H, J=7.8, 8.1Hz, Ar-H, H-6 of quinoxaline), 8.45 (d, 1H, J=8.4Hz, Ar-H, H-8 of quinoxaline), 8.59 (d, 1H, J=8.1Hz, Ar-H, H-5 of quinoxaline), 10.02 (s, 1H, Ar-H, N-CH=N), 10.54 (s, 1H, -NH, D2O exchangeable); 13C NMR (DMSO-d6, 100 MHz) delta (ppm): 38.9, 55.4, 105.4, 109.4, 111.8, 118.0, 118.5, 123.1, 124.0, 128.3 (2), 130.0, 138.7, 139.4, 140.3, 142.3, 147.7, 159.9, 165.5; DEPT (DMSO-d6, 100 MHz) delta (ppm): 38.9 (1CH3), 55.4 (1CH2), 105.3, 109.4, 111.8, 118.0, 118.5, 128.3 (2), 130.0, 138.7 (9CH); Anal. Calcd. for C19H15N7O2S (405.43): C, 56.29; H, 3.73; N, 24.18. Found: C, 56.42; H, 3.71; N, 24.39 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17641-08-6, its application will become more common.

Reference:
Article; Ibrahim; Taghour; Metwaly; Belal; Mehany; Elhendawy; Radwan; Yassin; El-Deeb; Hafez; ElSohly; Eissa; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 117 – 134;,
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Related Products of 125414-41-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 125414-41-7 as follows.

2-(tert-butoxycarbonylamino)propane-l ,3-diyl ditetradecanoate To a solution of tetradecanoic acid (1.051 g) in dichloromethane (10 mL) at 00C were added tert-butyl l,3-dihydroxypropan-2-ylcarbamate (0.40 g), 4-(dimethylamino)pyridine (0.562 g), N-methylmorpholine (1.150 mL), and l-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride (0.882 g). The mixture was stirred at room temperature overnight. The mixture was partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane. The extract were dried over Na2SO4, filtered, and concentrated. The concentrate was purified by flash chromatography (1 :10 ethyl acetate/hexanes). MS (ESI) m/z 512.4 (M-CO2-tert-butyl+l)+.

According to the analysis of related databases, 125414-41-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/129385; (2009); A1;,
Amide – Wikipedia,
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Related Products of 16982-21-1,Some common heterocyclic compound, 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, molecular formula is C4H7NO2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 1-bromo-3-methylbutan-2-one (1.1 g, 6.66 mmol), ethyl thioxamate (600 mg, 4.51 mmol) in 5.0 mL ethanol was refluxed overnight. After the completion of the reaction the solvent was removed and the crude mixture was dissolved in ethyl acetate. The organic layer was washed with water, brine and was dried under sodium sulfate. Evaporation of the solvent produced the desired product mixed with impurities which was used for the next step without further purification (400 mg, 30% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-amino-2-thioxoacetate, its application will become more common.

Reference:
Patent; LaVoie, Edmond J.; Parhi, Ajit; Pilch, Daniel S.; Zhang, Yongzheng; Kaul, Malvika; US2015/133465; (2015); A1;,
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Reference of 5900-59-4,Some common heterocyclic compound, 5900-59-4, name is 2-Amino-4-chlorobenzamide, molecular formula is C7H7ClN2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE A To a mixture of 0.34 g of 2-amino-4-chlorobenzamide, 0.57 g of monochloroacetic acid, 0.90 g of sodium iodide and 0.24 g of magnesium oxide was added 2 ml of dimethylformamide and the mixture was stirred at a temperature between 90¡ã and 100¡ã C. for 2.5 hours. After cooling, the reaction mixture was poured into 50 ml of a 2.6percent aqueous sodium carbonate solution. The resulting precipitates were filtered off and the filtrate was extracted with 50 ml of chloroform. The aqueous layer was acidified with concentrated hydrochloric acid to precipitate crystals. The crystals were collected by filtration and recrystallized from aqueous methanol to obtain 0.20 g of N-(2-carbamoyl-5-chlorophenyl)glycine as needles having a melting point of 217¡ã-222¡ã C. (decomposition). Elemental Analysis for C9 H9 O3 N2 Cl: Calcd.(percent): C, 47.28; H, 3.97; N, 12.25. Found (percent): C, 47.11; H, 3.74; N, 12.32.

The synthetic route of 5900-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Seiyaku Co., Ltd.; US4297357; (1981); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 20348-09-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 20348-09-8, name is 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 2H-pyrido[3,2-b][1 ,4]oxazin-3(4H)-one (45.0 g, 300 mmol) in DMF (360 mL) at 20 C was added NBS (74.7 g, 420 mmol) in one portion, and the resulting brownish suspension was heated at 50 C for 20 hours. The mixture was cooled to 25 C, and the content was poured into stirred water (1 L) in a 3 L flask fitted with an overhead mechanical stirrer. The resulting aqueous suspension was stirred at room temperature for 30 minutes followed by filtration. The yellowish cake was washed with 10% Na2S203 solution (100 mL) followed by water (2 x 100 mL). The cake was aspirated at room temperature under house vacuum overnight. The solids were washed with Et20 (100 mL), aspirated under house vacuum at room temperature for 18 hours, and then dried under high vacuum at 50 C for 72 hours to afford the title compound (65.30 g) as a light tan-colored powdery solid. LC-MS (ES) m/z = 229, 231 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 4.68 (s, 2H), 7.66 (d, J = 2.0 Hz, 1 H), 8.02 (d, J = 2.0 Hz, 1 H), 1 1 .44 (br. s., 1 H).

The synthetic route of 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; MEDINA, Jesus Raul; TIAN, Xinrong; NG DI MARCO, Christina; GRAYBILL, Todd L.; HEERDING, Dirk A.; LI, William Hoi Hong; MANGATT, Biju; MARTYR, Cuthbert D.; RIVERO, Raphael Anthony; (570 pag.)WO2019/49061; (2019); A1;,
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Reference of 25900-61-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 25900-61-2, name is 3-Amino-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 9; N-(2-Diethylamino-ethyl)-4-(3-indan-5-yl-3H-[1 ,2,3]triazolo[4,5-d]- pyrimidin-5-ylamino)-benzamide (7); To a solution of 2,4-dichloro-5-nitropyrimidine (25.0 mg, 0.13 mmol) in THF (0.2 mL) was added a solution of 3-amino-N-methyl-benzamide (19.5 mg, 0.13 mmol) in isopropyl alcohol (0.5 mL)/dimethylformarnide (0.3 mL), and CsHCO3 (25.2 mg, 0.13 mmol) in water (0.016 mL total volume). The mixture was stirred at rt for 1.5 hr at which time 4-amino-N-(2-diethylamino-ethyl)-benzamideEtaCl (procainamide hydrochloride) (38.9 mg, 0.14 mmol) in isopropyl alcohol (0.5 mL)/dimethylformamide (0.3 mL) was added. The mixture was stirred at 50C for 20 hr, cooled to rt, and acetic acid (0.1 mL) was added. To the resulting slurry was added Zn dust (45 mg, 0.69 mmol); after stirring for 15 min at rt, the reaction solution was loaded onto a 1 g silica gel SPE cartridge and eluted with 6 mL of MeOH. The eluent was concentrated at reduced pressure, dried at approximately 1 mm Hg for 18 hr, and re-suspended in MeOH (1.0 mL). To this slurry was added HOAc (0.05 mL) and sodium nitrite (0.09 g, 1.3 mmol) in water (total volume 0.2 mL). The mixture was stirred at rt for 11 hr, loaded onto a 1 g C-18 SPE cartridge, and eluted with 6 mL of MeOH. The eluent was concentrated and the resulting residue was purified by reverse-phase liquid chromatography using a gradient of 90:10 (water:acetonitrile, with 0.1% TFA) to 10:90 (wateracetonitrile, with 0.1% TFA) to furnish (7) (0.0128 g, 0.018 mmol) as the bis TFA salt. HRMS (ES-TOF) calcd. for C25H30N9O2 m/z 488.2522 (M+H),+ found: 488.2514

The synthetic route of 3-Amino-N-methylbenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/76442; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1444-94-6, name is 1,2-Cyclohexanedicarboximide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1444-94-6, Application In Synthesis of 1,2-Cyclohexanedicarboximide

General procedure: To a suspension of corresponding cyclic imide 1a-1k (4mmol), potassium carbonate (4.4mmol) in DMF (5mL), 1-bromo-4-chlorobutane (1,2-dibromoethane (5 eq) for 2l, 1-bromo-3-chloropropane for 2m, 1-bromo-5-chloropentane for 2n) (4.4mmol) was added dropwise at 0C. The mixture was stirred at room temperature overnight and then partitioned between ethyl acetate (EA, 20mL) and water (30mL). The organic layer was washed successively with water (3¡Á30mL), saturated brine, and dried over anhydrous Na2SO4. The solvent was evaporated under vacuum and the residue was purified by column chromatography using petroleum ether(PE): EA (8:1) as eluent to give 2a-2n.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,2-Cyclohexanedicarboximide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Mingshuo; Wang, Yu; Yang, Feipu; Wu, Chunhui; Wang, Zhen; Ye, Bin; Jiang, Xiangrui; Zhao, Qingjie; Li, Jianfeng; Liu, Yongjian; Zhang, Junchi; Tian, Guanghui; He, Yang; Shen, Jingshan; Jiang, Hualiang; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 74 – 85;,
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Amide – an overview | ScienceDirect Topics